14248-23-8Relevant academic research and scientific papers
The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling
Hayashi, Ryutaro,Shimizu, Akihiro,Yoshida, Jun-Ichi
, p. 8400 - 8403 (2016/07/27)
Electrochemical oxidation of toluene derivatives in the presence of a sulfilimine gave benzylaminosulfonium ions as stabilized benzyl cation pools, which reacted with subsequently added aromatic nucleophiles to give the corresponding cross-coupling produc
Pd(II)-catalyzed primary-C(sp3)-H acyloxylation at room temperature
Rit, Raja K.,Yadav, M. Ramu,Sahoo, Akhila K.
supporting information; experimental part, p. 3724 - 3727 (2012/08/28)
With the aid of a novel S-methyl-S-2-pyridyl-sulfoximine (MPyS) directing group (DG), the unactivated primary β-C(sp3)-H bond of MPyS-N-amides oxidizes at room temperature. The catalytic conditions are applicable to the diacetoxylation of primary β,β′-C(sp 3)-H bonds, and the carboxylic acid solvent is pivotal in the formation of the C-O bond. The MPyS-DG cleaves from the oxidation products and is recovered. This method provides convenient access to α,α′- disubstituted-β-hydroxycarboxylic acids.
Trialkylsilyl triflimides as easily tunable organocatalysts for allylation and benzylation of silyl carbon nucleophiles with non-genotoxic reagents
Mendoza, Oscar,Rossey, Guy,Ghosez, Léon
supporting information; experimental part, p. 2571 - 2575 (2010/06/21)
Trialkylsilyl triflimides generated in situ are unique catalysts for the electrophilic benzylation or allylation of trialkylsilylenol ethers or allyl trialkylsilanes with non-genotoxic alkylating reagents such as benzyl and allyl acetates. In most cases the reactions are fast at room temperature and yields are high. The reaction works particularly well with electron-rich benzyl donors including derivatives of pyrrole, indole and furane.
Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers
Nishimoto, Yoshihiro,Saito, Takahiro,Yasuda, Makoto,Baba, Akio
experimental part, p. 5462 - 5471 (2009/12/01)
The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.
Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide
Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
, p. 4931 - 4934 (2008/03/27)
Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of α-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl chloride, and allylsilane or alkynylsilane.
Magnesium trifluoromethanesulfonimide(triflimide) promoted substitution reactions of allylic and benzylic acetates. Magnesium triflimide as a substitute for magnesium perchlorate.
Grieco, Paul A.,Handy, Scott T.
, p. 2645 - 2648 (2007/10/03)
Magnesium triflimide(10 mol% in methylene chloride) is a convenient catalyst for the nucleophilic substitution of allylic and benzylic acetates, and constitutes a useful alternative to magnesium perchlorate.
Benzylation of ketones by a novel decarboxylative coupling reaction of benzylic chloroformate and silyl enol ether
Takeda, Kazuyoshi,Ayabe, Akira,Kawashima, Hideki,Harigaya, Yoshihiro
, p. 951 - 952 (2007/10/02)
In the presence of silver triflate, benzylic chloroformates react with silyl enol ethers to afford benzylated ketones by the decarboxylative coupling in good yields, whereas in the presence of various Lewis acids, yields of the product were poor under the same reaction conditions.
Radical Substitution on the Sulphur of Thioester Group
Tada, Masaru,Uetake, Tomohiro,Matsumoto, Mitsuhiro
, p. 1408 - 1409 (2007/10/02)
Intermolecular reaction of an organo-radical with thioester gives the sulphide, which is formed by the sulphur centred substitution of acyl groups with a nucleophilic organo-radical, but no displacement of S-alkyl groups with the organo-radical takes place.
SILVER TRIFLATE-PROMOTED COUPLING REACTIONS OF BENZYLIC AND ALLYLIC SULFIDES WITH O-SILYLATED ENOLATES OF KETONES AND ESTERS, A SYNTHESIS OF (+/-)-AR-TURMERONE
Takeda, Kazuyoshi,Torii, Katsumi,Ogura, Haruo
, p. 265 - 266 (2007/10/02)
Reactions of benzylic and allylic sulfides 1 having 5-mercapto-1-phenyl-1H-tetrazolyl group with O-silylated ketone and ester enolates 2 in the presence of silver triflate gave coupling products 3 in good yield. (+/-)-ar-turmerone was synthesized by this
